Stereoelectronic contributions to long-range 1H-1H coupling constants

Journal of Physical Chemistry A

Volumn 106, Issue 34, 2002, Pages 7834-7843

  Sproviero, Eduardo M ^a   Burton, Gerardo ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

NATURAL BOND ORBITAL (NBO) ANALYSIS; STEREOELECTRONIC INTERACTIONS;

HYDROGEN BONDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLARIZATION; PROTONS;

HYDROCARBONS;

EID: 0037194583     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp020197c     Document Type: Article

References (39)

1. A preliminary account of this work was presented at the 12th National Symposium of Organic Chemistry (XII SINAQO), Los Cocos, Argentina, November 1999. Abstract published in Molecules [online computer file] 2000, 5, 539.
2. Pople, J.A.; Schneider, W.G.; Bernstein, H.J. High-Resolution NMR; McGraw-Hill: New York, 1959.
3. Ramsey, N.F. Phys. Rev. 1953, 91, 303.
4. (a) Lemieux, R.U.; Kullnig, R.K.; Berstein, H.J.; Schneider, W.G. J. Am. Chem. Soc. 1957, 79, 1005.
5. (b) Karplus, M. J. Chem. Phys. 1959, 30, 11.
6. McConnell, H.M. J. Mol. Spectrosc. 1957, 1, 11.
7. Hoffman, R.A. Mol. Phys. 1958, 1, 326.
8. Barfield, M.; Chakrabarti, B. Chem. Rev. 1969, 69, 757.
9. Murrel, J.N. Prog. NMR Spectrosc. 1970, 6, 1.
10. Günther, H.; Jikeli, G. Chem. Rev. 1977, 77, 599.
11. Kowalewski, J. Prog. NMR Spectrosc. 1977, 11, 1.
12. Engelmann, R.; Facelli, J.C.; Contreras, R.H. Theor. Chim. Acta 1981, 59, 17.
13. Engelmann, R.; Contreras, R.H. Int. J. Quantum Chem. 1983, 23, 1033.
14. Contreras, R.H.; Natiello, M.A.; Scuseria, G.E. Magn. Reson. Rev. 1985, 9, 239.
15. Contreras, R.H.; Ruiz de Azúa, M.C.; Giribet, C.G.; Ferraro, M.B.; Diz, A.C. In Nuevas Tendencias-Química Teórica; Fraga, S., Ed.; CSIC: Madrid, 1989; Vol. 2, Chapter 16.
16. Parr, W.J.E.; Schaefer, T. Acc. Chem. Res. 1980, 13, 400.
17. Dewar, M.J.S.; Dougherty, R.C. The PMO Theory of Organic Chemistry; Plenum: New York, 1975.
18. Dewar, M.J.S. J. Am. Chem. Soc. 1984, 106, 669.
19. Reed, E.; Curtiss, L.A.; Weinhold, F.A. Chem. Rev. 1988, 88, 899.
20. Reed, A.E.; Weinhold, F. Isr. J. Chem. 1991, 31, 277.
21. Edison, S.; Markley, J.L.; Weinhold, F. J. Biomol. NMR 1994, 4, 519.
22. Esteban, A.L.; Galache, M.P.; Mora, F.; Díez, E.; Casanueva, J.; San Fabián, J.; Barone, V.; Peralta, J.E.; Contreras, R.H. J. Phys. Chem. A 2001, 105, 5298.
23. Wilkens, S.J.; Westler, W.M.; Markley, J.L.; Weinhold, F. J. Am. Chem. Soc. 2001, 123, 12026.
24. Peralta, J.E.; Contreras; R.H.; Snyder, J.P. Chem. Commun. 2000, 2025.
25. See, for example: (a) Suarez, D.; Sordo, T.L.; Sordo, J.A. J. Am. Chem. Soc. 1996, 118, 9850.
26. (b) Salzner, U. J. Org. Chem. 1995, 60, 986.
27. Barfield, M. J. Chem. Phys. 1964, 41, 3825.
28. Diz, C.; Ruiz de Azua, M.C.; Giribet, C.G.; Contreras, R.H. Int. J. Quantum Chem. 1990, 27, 663.
29. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Zakrzewski, V.G.; Montgomery, J.A.; Stratmann, R.E.; Burant, J.C.; Dapprich, S.; Millam, J.M.; Daniels, A.D.; Kudin, K.N.; Strain, M.C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G.A.; Ayala, P.Y.; Cui, Q.; Morokuma, K.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Cioslowski, J.; Ortiz, J.V.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P.M.W.; Johnson, B.G.; Chen, W.; Wong, M.W.; Andres, J.L.; Head-Gordon, M.; Replogle, E.S.; Pople, J.A. Gaussian 98, Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
30. (a) Lazzeretti, P.; Zanasi, R. J. Chem. Phys. 1982, 77, 2448.
31. (b) Lazzeretti, P. Int. J. Quantum Chem. 1979, 15, 181.
32. (c) Lazzeretti, P. J. Chem. Phys. 1979, 71, 2514.
33. Contreras, R.H.; Peralta, J.E. Prog. NMR Spectrosc. 2000, 37, 321.
34. Glendening, E.D.; Reed, A.E.; Carpenter, J.E.; Weinhold, F. NBO, version 3.1.
35. Jörgensen, P.; Simons, J. Second Quantization Based Methods in Quantum Chemistry; Academic Press: New York, 1981; Chapter 6.
36. Sproviero, E.M.; Ferrara, A.; Contreras, R.H.; Burton, G. J. Chem. Soc., Perkin Trans. 2 1996, 933, and references therein.
37. (a) Karplus, M. J. Chem Phys. 1960, 33, 1842.
38. (b) Karplus, M. J. Chem. Phys. 1969, 50, 3133.
39. Barfield, M.; Dean, A.M.; Fallick, C.J.; Spear, R.J.; Sternhell, S.; Westerman, P.W. J. Am. Chem. Soc. 1975, 97, 1482.